Organic electroluminescent materials and devices

Abstract

Provided are organometallic compounds having a structure of Formula I: Also provided are formulations including these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.

What is claimed is: 
     
         1 . A compound having a structure of Formula I: 
       
         
           
           
               
               
           
         
         wherein:
 rings A, and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; 
 moiety C is a 5-membered or 6-membered carbocyclic or heterocyclic ring if present, otherwise ring A and ring B are fused together if moiety C is not present; 
 each of Z A  and Z B  is independently C or N; 
 one of Z A  or Z B  is C; 
 M 1  and M 2  are each independently Pt or Pd; 
 n is 1, 2, or 3; 
 each L, the same or different, is independently a monodentate, bidentate, or tridentate ligand, but not a phosphine ligand; 
 each of R A , R B , and R C  independently represents zero, mono, or up to the maximum allowed number of substitutions; 
 each of R A , R B , and R C  is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
 any two adjacent R A , R B , or R C  can be joined or fused together to form a ring; and 
 at least one of the following is true:
 i) at least one L has three M-N bonds: 
 ii) at least one of rings A, B, or C, if present, comprises a 5-membered ring; 
 iii) at least one of rings A or B is a heterocyclic ring; or 
 iv) when ring C is not present and rings A and B form naphthalene or when ring Cis present and rings A, B, and C form anthracene, at least one R A  or R B  is a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. 
 
 
       
     
     
         2 . The compound of  claim 1 , wherein each of R A , R B , and R C  is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof. 
     
     
         3 . The compound of  claim 1 , wherein the compound has a structure of 
       
         
           
           
               
               
           
         
         wherein X 1  and X 2  are each independently C or N. 
       
     
     
         4 . The compound of  claim 3 , wherein X 1  and X 2  are both C. 
     
     
         5 . The compound of  claim 1 , wherein Z A  and Z B  are both C, or one of Z A  and Z B  is C and the other is N. 
     
     
         6 . The compound of  claim 1 , wherein ring A and ring B are both 6-membered rings. 
     
     
         7 . The compound of  claim 1 , wherein ring A is a 6-membered ring, and ring B is a 5-membered ring. 
     
     
         8 . The compound of  claim 1 , wherein ring C if present is a 5-membered ring or a 6-membered ring. 
     
     
         9 . The compound of  claim 1 , wherein n is 1 and each L is tridentate. 
     
     
         10 . The compound of  claim 9 , wherein each L is independently selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein X 1  to X 13  are each independently N or CR, each of R, and R 1  is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and any two adjacent R or R 1  can be joined or fused together to form a ring. 
       
     
     
         11 . The compound of  claim 1 , wherein an L has three M-N bonds. 
     
     
         12 . The compound of  claim 1 , wherein at least one L coordinates to M by an M-C bond. 
     
     
         13 . The compound of  claim 1 , wherein M 1  and M 2  are both Pt or both Pd. 
     
     
         14 . The compound of  claim 1 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         15 . The compound of  claim 1 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         wherein each X is independently O, S, Se, or NR; R and R Y  each are independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; two adjacent R, R A , R B , and R C  can be joined to form a ring; and each of L 1  and L 2  is a tridentate ligand. 
       
     
     
         16 . The compound of  claim 1 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         17 . A compound having a structure of Formula IV: 
       
         
           
           
               
               
           
         
         wherein:
 Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6  are each independently C or N; 
 M 1  and M 2  are each independently Pt or Pd; 
 each of moieties A1, B1, C1, A2, B2, and C2 is a monocylic or multicyclic ring structure comprising 5-membered and/or 6-membered carbocylic or heterocyclic rings; 
 
         wherein moiety Q is a linking group selected from: 
       
       
         
           
           
               
               
           
         
         wherein each X is independently O, S, or NR; 
         R A , R B , and R C  each independently represent zero, mono, or up to the maximum allowed number of substitutions; 
         each of R, R A , R B , R C , and R Q  is independently a hydrogen or a substituent, 
         and two adjacent R, R A , R B , and R C  can be joined to form a ring;
 each of R A1 , R B1 , R C1 , R A2 , R B2 , and R C2  independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring; 
 each of R A1 , R B1 , R C1 , R A2 , R B2 , and R C2  is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
 any two adjacent R A1 , R B1 , R C1 , R A2 , R B2 , or R C2  can be joined to form a ring; and 
 at least one of the following is true:
 a) at least one set of Z 1  to Z 3  or Z 4  to Z 6  are each N; 
 b) Q, comprises a 5-membered ring; 
 c) Q comprises a heterocyclic ring that is fused to exactly one other ring; 
 d) Q is naphthalene or anthracene wherein said naphthalene or anthracene comprises a substituent selected from the group consisting of deuterium, halogen, alkyl cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl alkoxy aryloxy amino, silyl germyl boryl selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. 
 
 
       
     
     
         18 . An organic light emitting device (OLED) comprising:
 an anode;   a cathode; and   an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound according to   
       
         
           
           
               
               
           
         
       
       wherein, in Formula I:
 rings A, and B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; 
 moiety C is a 5-membered or 6-membered carbocyclic or heterocyclic ring if present, otherwise ring A and ring B are fused together if moiety C is not present; 
 each of Z A  and Z B  is independently C or N; 
 one of Z A  or Z B  is C; 
 M 1  and M 2  are each independently Pt or Pd; 
 n is 1, 2, or 3; 
 each L, the same or different, is independently a monodentate, bidentate, or tridentate ligand, but not a phosphine ligand; 
 each of R A , R B , and R C  independently represents zero, mono, or up to the maximum allowed number of substitutions; 
 each of R A , R B , and R C  is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
 any two adjacent R A , R B , or R C  can be joined or fused together to form a ring; and 
 at least one of the following is true;
 i) at least one L has three M-N bonds; 
 ii) at least one of rings A, B, or C, if present, comprises a 5-membered ring; 
 iii) at least one rings A or B is a heterocyclic ring; or 
 iv) when ring C is not present and rings A and B form naphthalene or when ring Cis present and rings A, B, and C form anthracene, at least one R A  or R B  a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
 
 
       wherein, in Formula IV;
 Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6  are each independently C or N; 
 M 1  and M 2  are each independently Pt or Pd; 
 each of moieties A1, B1, C1, A2, B2, and C2 is a monocyclic or multicyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings; 
 wherein moiety Q is a linking group selected from: 
 
       
         
           
           
               
               
           
         
         wherein each X is independently O, S, or NR; 
         R A , R B , and R C  each independently represent zero, mono, or up to the maximum allowed number of substitutions; 
         each of R, R A , R B , R C , and R Q  is independently a hydrogen or a substituent, 
         and two adjacent R, R A , R B , and R C  can be joined to form a ring; 
         one of M 1  or M 2  bond to a carbon ring atom of moiety Q;
 each of R A1 , R B1 , R C1 , R A2 , R B2 , and R C2  independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring; 
 each of R A1 , R B1 , R C1 , R A2 , R B2 , and R C2  is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; 
 any two adjacent R A1 , R B1 , R C1 , R A2 , R B2 , or R C2  can be joined to form a ring and at least one of the following is true;
 a) at least one set of 2ª to Z′ or Z A  to Ze are each N; 
 b) Q, comprises a 5-membered ring; 
 e) Q comprises a heterocyclic ring that is fused to exactly one other ring: 
 d) Q is naphthalene or anthracene wherein said naphthalene or anthracene comprises a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl sulfinyl, sulfonyl phosphino, and combinations thereof. 
 
 
       
     
     
         19 . The OLED of  claim 18 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene). 
     
     
         20 . The OLED of  claim 19 , wherein the host is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and combinations thereof.